cyclododecane-1,2-dicarboxylic acid dipyridin-2-yl-methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: cyclododecane-1,2-dicarboxylic acid dipyridin-2-yl-methyl ester
• 英文别名: Bis(pyridin-2-ylmethyl) cyclododecane-1,2-dicarboxylate
• 化学式: C₂₆H₃₄N₂O₄
• 分子量: 438.567
• InChiKey: HZRARWZCHJGFOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-吡啶甲醇 、 环十二碳炔 、 一氧化碳 在 dodecacarbonyltetrarhodium(0) 作用下， 以 甲苯 为溶剂， 100.0 ℃ 、303.97 kPa 条件下， 反应 20.0h， 以57%的产率得到cyclododecane-1,2-dicarboxylic acid dipyridin-2-yl-methyl ester
  参考文献：
  名称：

  Chelation-Assisted Transformation:  Synthesis of 1,4-Dicarboxylate Esters by the Rh-Catalyzed Carbonylation of Internal Alkynes with Pyridin-2-ylmethanol

  摘要：

  The reaction of internal alkynes 1 with CO and pyridin-2-ylmethanol (2) in the presence of Rh4(CO) 12 results in a double-hydroesterification leading to 1,4-dicarboxylate esters 3. The reaction does not proceed via two consecutive hydroesterifications of alkynes, but the intermediacy of ketene intermediates is proposed. The coordination of the pyridine nitrogen in 2 to rhodium is essential for the reaction to proceed.

  DOI：

  10.1021/ol060715s

文献信息

• Chelation-Assisted Transformation:  Synthesis of 1,4-Dicarboxylate Esters by the Rh-Catalyzed Carbonylation of Internal Alkynes with Pyridin-2-ylmethanol
  作者：Satoshi Inoue、Kazuhiko Yokota、Hiroto Tatamidani、Yoshiya Fukumoto、Naoto Chatani

  DOI：10.1021/ol060715s

  日期：2006.6.1

  The reaction of internal alkynes 1 with CO and pyridin-2-ylmethanol (2) in the presence of Rh4(CO) 12 results in a double-hydroesterification leading to 1,4-dicarboxylate esters 3. The reaction does not proceed via two consecutive hydroesterifications of alkynes, but the intermediacy of ketene intermediates is proposed. The coordination of the pyridine nitrogen in 2 to rhodium is essential for the reaction to proceed.